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Organic letters DOI:10.1021/ol202276h

Diastereoselective control of intramolecular aza-Michael reactions using achiral catalysts.

Publication Type

Journal Article

Year of Publication

2011

Authors

Zhong, C, Wang, Y, Hung, AW, Schreiber, SL, Young, DW

Journal

Organic letters

Volume

13

Issue

20

Pages

5556-9

Date Published

2011/10/21

ISSN

1523-7060

Abstract

An intramolecular aza-Michael reaction with a Cbz carbamate and an enone is reported to result in 3,5-disubstituted nitrogen-containing heterocycles. Either cis or trans isomers were obtained selectively using chiral substrates and an achiral Pd(II) complex or strong Brønsted acid catalysis. A range of substrates undergoes these selective transformations. Functionalization of the resulting products yielding bicyclic heterocycles is also demonstrated.